Water → 5-{4-[2-(1-Methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione

HRID 4387

反応式

HRID 4387 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2([CH3:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:23][CH:24]=1.O>CN(C)C=O>[CH3:31][C:25]1([C:22]2[O:23][CH:24]=[C:20]([CH2:19][O:3][C:4]3[CH:17]=[CH:16][C:7]([CH2:8][CH:9]4[S:13][C:12](=[O:14])[NH:11][C:10]4=[O:15])=[CH:6][CH:5]=3)[N:21]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 201524064-Chloromethyl-2-(1-methylcyclohexyl)oxazole

生成物 1

HCID 137139035-{4-[2-(1-Methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

60% sodium hydride in oil (1.32 g) was added to solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (3.35 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred for 30 minutes. Then, solution of 4-chloromethyl-2-(1-methylcyclohexyl)oxazole (3.85 g) in N,N-dimethylformamide (5 ml) was added dropwise thereto at room temperature. After being stirred at 60° C. for 1 hour, the reaction solution was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (70 g). Elution with hexaneethyl acetate (2:1, V/V) gave 5-{4-[2-(1-methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione as an oily substance. A solution of sodium 2-ethylhexanoate in isopropanol (2N, 3 ml) was added to the oily substance, and treated with ether. The crystals which separated out were collected by filtration to give 5- {4-[2-(1-methylcyclohexyl)-4-oxazolylmethoxy]benzyl}-2,4-thiazolidinedione.sodium salt (2.3 g, 36.3%). Recrystallization from methanol afforded colorless plates. m.p. 285°-287° C. (decomp.) Elemental analysis for C21H23N2O4SNa, Calcd.: C, 59.70; H, 5.49; N, 6.63. Found: C, 59.76; H, 5.56; N, 6.82.

後処理

  1. customat room temperature
  2. stirringAfter being stirred at 60° C. for 1 hour
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe oily residue was chromatographed on a column of silica gel (70 g)
  8. washElution with hexaneethyl acetate (2:1, V/V)

出典と根拠

ORDレコード
ord-1600130bf31e4d3497fdf571ee839211
出典データセット
uspto-grants-1988_02
特許番号
US04725610

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